JP6640739B2 - 亜硝酸で後処理される複合ポリアミド膜 - Google Patents
亜硝酸で後処理される複合ポリアミド膜 Download PDFInfo
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- JP6640739B2 JP6640739B2 JP2016565406A JP2016565406A JP6640739B2 JP 6640739 B2 JP6640739 B2 JP 6640739B2 JP 2016565406 A JP2016565406 A JP 2016565406A JP 2016565406 A JP2016565406 A JP 2016565406A JP 6640739 B2 JP6640739 B2 JP 6640739B2
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- amine
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- hydroxyl
- amino
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- 239000004952 Polyamide Substances 0.000 title claims description 52
- 229920002647 polyamide Polymers 0.000 title claims description 52
- 239000012528 membrane Substances 0.000 title claims description 35
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 title claims description 25
- 239000002131 composite material Substances 0.000 title claims description 10
- -1 amine compound Chemical class 0.000 claims description 52
- 150000001412 amines Chemical class 0.000 claims description 44
- 239000000178 monomer Substances 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 35
- 150000001266 acyl halides Chemical class 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 150000002431 hydrogen Chemical group 0.000 claims description 18
- 150000003335 secondary amines Chemical class 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 239000010409 thin film Substances 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 150000003839 salts Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 238000012695 Interfacial polymerization Methods 0.000 claims description 7
- 150000003512 tertiary amines Chemical class 0.000 claims description 7
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 6
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 claims description 5
- 229940018563 3-aminophenol Drugs 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- BAHPQISAXRFLCL-UHFFFAOYSA-N 2,4-Diaminoanisole Chemical compound COC1=CC=C(N)C=C1N BAHPQISAXRFLCL-UHFFFAOYSA-N 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical group CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
- WFZAJJVJZLVLKM-UHFFFAOYSA-N 2-[3-amino-5-(carboxymethyl)phenyl]acetic acid Chemical compound NC1=CC(CC(O)=O)=CC(CC(O)=O)=C1 WFZAJJVJZLVLKM-UHFFFAOYSA-N 0.000 claims description 3
- WFNVGXBEWXBZPL-UHFFFAOYSA-N 3,5-diaminophenol Chemical compound NC1=CC(N)=CC(O)=C1 WFNVGXBEWXBZPL-UHFFFAOYSA-N 0.000 claims description 3
- DCOZZPQKAZEDBO-UHFFFAOYSA-N 3-N,3-N-dimethylbenzene-1,3,5-triamine Chemical compound CN(C1=CC(=CC(=C1)N)N)C DCOZZPQKAZEDBO-UHFFFAOYSA-N 0.000 claims description 3
- SHCTVTZAVRBWEL-UHFFFAOYSA-N 3-amino-5-hydroxybenzenesulfonic acid Chemical compound NC1=CC(O)=CC(S(O)(=O)=O)=C1 SHCTVTZAVRBWEL-UHFFFAOYSA-N 0.000 claims description 3
- RSCVHPBMEDSBLL-UHFFFAOYSA-N 3-amino-5-methoxybenzenesulfonic acid Chemical compound COC1=CC(N)=CC(S(O)(=O)=O)=C1 RSCVHPBMEDSBLL-UHFFFAOYSA-N 0.000 claims description 3
- DBEMTZANGFGKMX-UHFFFAOYSA-N 3-amino-5-methoxybenzoic acid Chemical compound COC1=CC(N)=CC(C(O)=O)=C1 DBEMTZANGFGKMX-UHFFFAOYSA-N 0.000 claims description 3
- HHSBHVJQXZLIRW-UHFFFAOYSA-N 3-n,3-n-dimethylbenzene-1,3-diamine Chemical compound CN(C)C1=CC=CC(N)=C1 HHSBHVJQXZLIRW-UHFFFAOYSA-N 0.000 claims description 3
- PDCMTKJRBAZZHL-UHFFFAOYSA-N 5-aminobenzene-1,3-diol Chemical compound NC1=CC(O)=CC(O)=C1 PDCMTKJRBAZZHL-UHFFFAOYSA-N 0.000 claims description 3
- FLDIDKTWHOYFMG-UHFFFAOYSA-N 5-methoxybenzene-1,3-diamine Chemical compound COC1=CC(N)=CC(N)=C1 FLDIDKTWHOYFMG-UHFFFAOYSA-N 0.000 claims description 3
- SUBDSNMSVKJERE-UHFFFAOYSA-N C(C)(C)(C)[Si](OC=1C=C(N)C=C(C1)O[Si](C)(C)C(C)(C)C)(C)C Chemical compound C(C)(C)(C)[Si](OC=1C=C(N)C=C(C1)O[Si](C)(C)C(C)(C)C)(C)C SUBDSNMSVKJERE-UHFFFAOYSA-N 0.000 claims description 3
- CAZOALJANAHILR-UHFFFAOYSA-N N-[3-amino-5-(3-oxobutanoylamino)phenyl]-3-oxobutanamide Chemical compound CC(=O)CC(=O)Nc1cc(N)cc(NC(=O)CC(C)=O)c1 CAZOALJANAHILR-UHFFFAOYSA-N 0.000 claims description 3
- FZRKAZHKEDOPNN-UHFFFAOYSA-N Nitric oxide anion Chemical compound O=[N-] FZRKAZHKEDOPNN-UHFFFAOYSA-N 0.000 claims description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 3
- XIWMTQIUUWJNRP-UHFFFAOYSA-N amidol Chemical compound NC1=CC=C(O)C(N)=C1 XIWMTQIUUWJNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 claims description 3
- GGXAKQQKCYFCHS-UHFFFAOYSA-N n-(4-aminophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(N)C=C1 GGXAKQQKCYFCHS-UHFFFAOYSA-N 0.000 claims description 3
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 claims description 3
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- KWMZZAAUFPJVBL-UHFFFAOYSA-N 1-N,1-N,3-N,3-N-tetramethylbenzene-1,3,5-triamine Chemical compound CN(C1=CC(=CC(=C1)N)N(C)C)C KWMZZAAUFPJVBL-UHFFFAOYSA-N 0.000 claims description 2
- HYNQTSZBTIOFKH-UHFFFAOYSA-N 2-Amino-5-hydroxybenzoic acid Chemical compound NC1=CC=C(O)C=C1C(O)=O HYNQTSZBTIOFKH-UHFFFAOYSA-N 0.000 claims description 2
- RWELBGJOASPFQO-UHFFFAOYSA-N C(C)(C)(C)[Si](OC=1C=C(C=C(C1)O[Si](C)(C)C(C)(C)C)CCN)(C)C Chemical compound C(C)(C)(C)[Si](OC=1C=C(C=C(C1)O[Si](C)(C)C(C)(C)C)CCN)(C)C RWELBGJOASPFQO-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 33
- 229920000642 polymer Polymers 0.000 description 13
- 239000011248 coating agent Substances 0.000 description 11
- 238000000576 coating method Methods 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012954 diazonium Substances 0.000 description 6
- 238000001728 nano-filtration Methods 0.000 description 6
- 238000001223 reverse osmosis Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 150000001989 diazonium salts Chemical class 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 229940018564 m-phenylenediamine Drugs 0.000 description 5
- UWCPYKQBIPYOLX-UHFFFAOYSA-N benzene-1,3,5-tricarbonyl chloride Chemical compound ClC(=O)C1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 UWCPYKQBIPYOLX-UHFFFAOYSA-N 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 150000003141 primary amines Chemical group 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012454 non-polar solvent Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- QPEJHSFTZVMSJH-UHFFFAOYSA-N 3-amino-5-hydroxybenzoic acid Chemical compound NC1=CC(O)=CC(C(O)=O)=C1 QPEJHSFTZVMSJH-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PQDKXEFHIYPZCK-UHFFFAOYSA-N C(C)(C)(C)[Si](OC=1C=C(C=C(C1)O[Si](C)(C)C(C)(C)C)CN)(C)C Chemical compound C(C)(C)(C)[Si](OC=1C=C(C=C(C1)O[Si](C)(C)C(C)(C)C)CN)(C)C PQDKXEFHIYPZCK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000012696 Interfacial polycondensation Methods 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000006149 azo coupling reaction Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- JSYBAZQQYCNZJE-UHFFFAOYSA-N benzene-1,2,4-triamine Chemical compound NC1=CC=C(N)C(N)=C1 JSYBAZQQYCNZJE-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000009501 film coating Methods 0.000 description 2
- 239000007888 film coating Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 2
- 238000001471 micro-filtration Methods 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229920002492 poly(sulfone) Polymers 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000000108 ultra-filtration Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- UKISWDCMNXICCV-UHFFFAOYSA-N 1-phenyl-2-propylbenzene;phosphoric acid Chemical compound OP(O)(O)=O.CCCC1=CC=CC=C1C1=CC=CC=C1 UKISWDCMNXICCV-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- 125000003504 2-oxazolinyl group Chemical class O1C(=NCC1)* 0.000 description 1
- UENRXLSRMCSUSN-UHFFFAOYSA-N 3,5-diaminobenzoic acid Chemical compound NC1=CC(N)=CC(C(O)=O)=C1 UENRXLSRMCSUSN-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004697 Polyetherimide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 125000000777 acyl halide group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- RPHKINMPYFJSCF-UHFFFAOYSA-N benzene-1,3,5-triamine Chemical compound NC1=CC(N)=CC(N)=C1 RPHKINMPYFJSCF-UHFFFAOYSA-N 0.000 description 1
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- DWSYMNWJOYKKCK-UHFFFAOYSA-N butyl diethyl phosphate Chemical compound CCCCOP(=O)(OCC)OCC DWSYMNWJOYKKCK-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MYTYKMBAJLQHLQ-UHFFFAOYSA-N butyl heptyl hexyl phosphate Chemical compound CCCCCCCOP(=O)(OCCCC)OCCCCCC MYTYKMBAJLQHLQ-UHFFFAOYSA-N 0.000 description 1
- DJQFQXHRKYELGT-UHFFFAOYSA-N butyl heptyl hydrogen phosphate Chemical compound CCCCCCCOP(O)(=O)OCCCC DJQFQXHRKYELGT-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- GEQHKFFSPGPGLN-UHFFFAOYSA-N cyclohexane-1,3-diamine Chemical compound NC1CCCC(N)C1 GEQHKFFSPGPGLN-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- YICSVBJRVMLQNS-UHFFFAOYSA-N dibutyl phenyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OC1=CC=CC=C1 YICSVBJRVMLQNS-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- VVOSATWFENUSTP-UHFFFAOYSA-N ethylbenzene;1-methoxy-2-(2-methoxyethoxy)ethane Chemical compound CCC1=CC=CC=C1.COCCOCCOC VVOSATWFENUSTP-UHFFFAOYSA-N 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 238000009292 forward osmosis Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000012510 hollow fiber Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000004797 ketoamides Chemical class 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- WUQGUKHJXFDUQF-UHFFFAOYSA-N naphthalene-1,2-dicarbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(C(=O)Cl)=CC=C21 WUQGUKHJXFDUQF-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000765 poly(2-oxazolines) Chemical class 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- SFENPMLASUEABX-UHFFFAOYSA-N trihexyl phosphate Chemical compound CCCCCCOP(=O)(OCCCCCC)OCCCCCC SFENPMLASUEABX-UHFFFAOYSA-N 0.000 description 1
- QMKYBPDZANOJGF-UHFFFAOYSA-N trimesic acid Natural products OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 1
- 150000005199 trimethylbenzenes Chemical class 0.000 description 1
- QJAVUVZBMMXBRO-UHFFFAOYSA-N tripentyl phosphate Chemical compound CCCCCOP(=O)(OCCCCC)OCCCCC QJAVUVZBMMXBRO-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- RXPQRKFMDQNODS-UHFFFAOYSA-N tripropyl phosphate Chemical compound CCCOP(=O)(OCCC)OCCC RXPQRKFMDQNODS-UHFFFAOYSA-N 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/12—Composite membranes; Ultra-thin membranes
- B01D69/125—In situ manufacturing by polymerisation, polycondensation, cross-linking or chemical reaction
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/12—Composite membranes; Ultra-thin membranes
- B01D69/125—In situ manufacturing by polymerisation, polycondensation, cross-linking or chemical reaction
- B01D69/1251—In situ manufacturing by polymerisation, polycondensation, cross-linking or chemical reaction by interfacial polymerisation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
- B01D67/0002—Organic membrane manufacture
- B01D67/0006—Organic membrane manufacture by chemical reactions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
- B01D67/0081—After-treatment of organic or inorganic membranes
- B01D67/0088—Physical treatment with compounds, e.g. swelling, coating or impregnation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
- B01D67/0081—After-treatment of organic or inorganic membranes
- B01D67/0093—Chemical modification
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/14—Dynamic membranes
- B01D69/141—Heterogeneous membranes, e.g. containing dispersed material; Mixed matrix membranes
- B01D69/142—Heterogeneous membranes, e.g. containing dispersed material; Mixed matrix membranes with "carriers"
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/56—Polyamides, e.g. polyester-amides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/10—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by other chemical means
- B05D3/107—Post-treatment of applied coatings
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/10—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by other chemical means
- B05D3/107—Post-treatment of applied coatings
- B05D3/108—Curing
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/48—Polymers modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/20—Manufacture of shaped structures of ion-exchange resins
- C08J5/22—Films, membranes or diaphragms
- C08J5/2287—After-treatment
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D177/00—Coating compositions based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Coating compositions based on derivatives of such polymers
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01D2323/00—Details relating to membrane preparation
- B01D2323/30—Cross-linking
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2323/00—Details relating to membrane preparation
- B01D2323/36—Introduction of specific chemical groups
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01D2323/40—Details relating to membrane preparation in-situ membrane formation
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/002—Forward osmosis or direct osmosis
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/02—Reverse osmosis; Hyperfiltration ; Nanofiltration
- B01D61/025—Reverse osmosis; Hyperfiltration
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/02—Reverse osmosis; Hyperfiltration ; Nanofiltration
- B01D61/027—Nanofiltration
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/14—Ultrafiltration; Microfiltration
- B01D61/145—Ultrafiltration
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/14—Ultrafiltration; Microfiltration
- B01D61/147—Microfiltration
Description
複合ポリアミド膜は、様々な流体分離において使用される。1つの一般的な部類の膜は、「薄フィルム」ポリアミド層でコーティングされた多孔質支持体を含む。薄フィルム層は、非混和性溶液から経時的に支持体上にコーティングされる多官能性アミン(例えば、m−フェニレンジアミン)モノマーと多官能性ハロゲン化アシル(例えば、トリメソイルクロライド)モノマーとの間の界面重縮合反応によって形成され得、例えば、Cadotteへの米国特許第4,277,344号を参照されたい。様々な構成物質が、コーティング溶液のうちの一方または両方に添加されて、膜性能を改善し得る。例えば、Mickolsへの米国特許第6,878,278号は、様々なトリ−ヒドロカルビルホスフェート化合物を含むコーティング溶液のうちの一方または両方への、広範囲の添加剤の添加を記載する。米国特許第2013/0287944号、米国特許第2013/0287945号、米国特許第2013/0287946号、国際公開第2013/048765号、及び国際公開第2013/103666号は、様々なトリ−ヒドロカルビルホスフェート化合物と組み合わせた、カルボン酸及びアミン−反応性官能基の両方を含む様々なモノマーの添加を記載する。
Zが、ヒドロキシル、アルコキシ、エステル、第二級または第三級アミン、及びケト−アミドから選択され、
Yが、水素、カルボン酸、スルホン酸またはその塩、ハロゲン、アミン、及び1〜12個の炭素原子を有するアルキル基から選択され、
A、A’、A’’、及びA’’’が、独立して、Z、水素、アミンから選択されるが、但し、A、A’、A’’、及びA’’’のうちの少なくとも1つが第一級または第二級アミンであり、かつY、A、またはA’’のうちの少なくとも1つが水素であるものとする。
Zが、ヒドロキシル(−OH)、アルコキシ(例えば1〜5の炭素を有するアルキル基、好ましくはメトキシ、−OCH3を含む)、エステル(例えば−O−CO−CH3)、第二級または第三級アミン(例えば、−NHR、−NRR’、式中、R及びR’が、好ましくは1〜5個の炭素原子を有するアルキル基である)、及びケト−アミド(例えば−NH−CO−CH2−CO−CH3)から選択され、
Yが、水素(−H)、カルボン酸(−COOH)、スルホン酸またはその塩(−SO3H)、ハロゲン(−F、−Cl、−Br、−I)、及び1〜12個の炭素原子を有するアルキル基から選択され、
A、A’、A’’、及びA’’’が、独立して、Z、水素、及びアミン(第一級、第二級、または第三級、しかし好ましくは1〜5個の炭素原子を有するアルキル基を含む第一級または第二級)から選択されるが、但し、A、A’、A’’、及びA’’’のうちの少なくとも1つがアミン(第一級または第二級)であり、かつY、A、またはA’’のうちの少なくとも1つが水素であるものとする。
(態様)
(請求項1)
多孔質支持体及びポリアミド層を含む複合ポリアミド膜を作製するための方法であって、
i)多官能性アミンモノマーを含む極性溶液及び多官能性ハロゲン化アシルモノマーを含む非極性溶液を多孔質支持体の表面に適用し、前記モノマーを界面重合して、ポリアミド層を形成するステップと、
ii)前記薄フィルムポリアミド層を亜硝酸に曝露するステップと、を含み、
前記方法は、
a)ステップi)の前記界面重合を、対象となるアミン化合物の存在下で実施すること、及び
b)対象となるアミン化合物を、ステップii)の前に、前記界面重合したポリアミド層に適用することのうちの少なくとも1つを特徴とし、
前記対象となるアミン化合物は、前記多官能性アミンモノマーと異なり、以下の式によって表され、
(化1)
式中、
Zが、ヒドロキシル、アルコキシ、エステル、第二級または第三級アミン、及びケト−アミドから選択され、
Yが、水素、カルボン酸、スルホン酸またはその塩、ハロゲン、アミン、及び1〜12個の炭素原子を有するアルキル基から選択され、
A、A’、A’’、及びA’’’が、独立して、Z、水素、アミンから選択されるが、但し、A、A’、A’’、及びA’’’のうちの少なくとも1つが第一級または第二級アミンであり、かつY、A、またはA’’のうちの少なくとも1つが水素であるものとする、方法。
(請求項2)
Z、及びA’またはA’’’のうちの少なくとも1つがヒドロキシルであるが、但し、AまたはYのうちの少なくとも1つが水素であるものとする、請求項1に記載の方法。
(請求項3)
Z、及びA’またはA’’’のうちの少なくとも1つが第二級または第三級アミンであるが、但し、AまたはYのうちの少なくとも1つが水素であるものとする、請求項1に記載の方法。
(請求項4)
Zがヒドロキシルまたはメトキシから選択され、Yが水素、ハロゲン、またはカルボン酸から選択され、A、A’、A’’、及びA’’’が独立して、水素及びアミンから選択されるが、但し、A、A’、A’’、及びA’’’のうちの少なくとも1つが第一級または第二級アミンであり、かつAまたはA’’のうちの少なくとも1つが水素であるものとする、請求項1に記載の方法。
(請求項5)
Zがヒドロキシルから選択され、A’がヒドロキシルから選択され、Aが水素であるが、但し、A’’、A’’’、またはYのうちの少なくとも1つが第一級または第二級アミンであるものとする、請求項1に記載の方法。
(請求項6)
Zがヒドロキシルから選択され、A’’’がヒドロキシルから選択され、Yが水素であるが、但し、A、A’、またはA’’のうちの少なくとも1つが第一級または第二級アミンであるものとする、請求項1に記載の方法。
(請求項7)
前記多官能性アミンが二官能性アミンである、請求項1に記載の方法。
(請求項8)
前記極性及び非極性溶液のうちの少なくとも1つが、以下の式によって表されるトリ−ヒドロカルビルホスフェート化合物を更に含み、
(化2)
式中、R 1 、R 2 、及びR 3 が、独立して、水素及び1〜10個の炭素原子を含むヒドロカルビル基から選択されるが、但し、R 1 、R 2 、及びR 3 のうちの1つよりも多くが水素であることはないものとする、請求項1に記載の方法。
(請求項9)
前記対象となるアミン化合物が、ステップi)の前記極性溶液内の前記多官能性アミンモノマーと混合される、請求項1に記載の方法。
(請求項10)
前記対象となるアミン化合物が、3,5−ジアミノフェノール、2,4−ジアミノフェノール、3−アミノフェノール、2−アミノフェノール、4−アミノフェノール、5−アミノベンゼン−1,3−ジオール、3−アミノ−5−ヒドロキシ安息香酸、3−アミノ−5−ヒドロキシベンゼンスルホン酸、5−メトキシベンゼン−1,3−ジアミン、4−メトキシベンゼン−1,3−ジアミン、3−メトキシアニリン、2−メトキシアニリン、4−メトキシアニリン、3−アミノ−5−メトキシ安息香酸、3−アミノ−5−メトキシベンゼンスルホン酸、N1,N1−ジメチルベンゼン−1,3−ジアミン、N1,N1−ジメチルベンゼン−1,3,5−トリアミン、N1,N1,N3,N3−テトラメチルベンゼン−1,3,5−トリアミン、N,N’−(5−アミノ−1,3−フェニレン)ビス
(3−オキソブタンアミド)、N−(4−アミノフェニル)−3−オキソブタンアミド、5−アミノ−1,3−フェニレンビス(2,2,2−トリフルオロアセテート)、5−アミノ−1,3−フェニレンジアセテート、3,5−ビス((tert−ブチルジメチルシリル)オキシ)アニリン、(3,5−ビス((tert−ブチルジメチルシリル)オキシ)フェニル)メタンアミン、及び2−(3,5−ビス((tert−ブチルジメチルシリル)オキシ)フェニル)エタンアミンのうちの少なくとも1つから選択される、請求項1に記載の方法。
Claims (9)
- 多孔質支持体及びポリアミド層を含む複合ポリアミド膜を作製するための方法であって、
i)多官能性アミンモノマーを含む極性溶液及び多官能性ハロゲン化アシルモノマーを含む非極性溶液を多孔質支持体の表面にコーティングし、前記モノマーを界面重合して、薄フィルムポリアミド層を形成するステップと、
ii)前記薄フィルムポリアミド層を亜硝酸に曝露するステップと、を含み、
前記方法は、
対象となるアミン化合物が前記ポリアミド層内に存在する残留酸塩化物基と反応するようにステップii)の前に前記対象となるアミン化合物を界面重合したポリアミド層にコーティングすることを特徴とし、
前記対象となるアミン化合物が前記多官能性アミンモノマーと異なり、以下の式によって表され、
Zが、ヒドロキシル、アルコキシ、エステル、第二級または第三級アミン、及びケト−アミドから選択され、
Yが、水素、カルボン酸、スルホン酸またはその塩、ハロゲン、アミン、及び1〜12個の炭素原子を有するアルキル基から選択され、
A、A’、A’’、及びA’’’が、独立して、Z、水素、アミンから選択されるが、但し、A、A’、A’’、及びA’’’のうちの少なくとも1つが第一級または第二級アミンであり、かつY、A、またはA’’のうちの少なくとも1つが水素であるものとし
前記極性及び非極性溶液のうちの少なくとも1つが、以下の式によって表されるトリ−ヒドロカルビルホスフェート化合物を更に含み、
- Z、及びA’またはA’’’のうちの少なくとも1つがヒドロキシルであるが、但し、AまたはYのうちの少なくとも1つが水素であるものとする、請求項1に記載の方法。
- Z、及びA’またはA’’’のうちの少なくとも1つが第二級または第三級アミンであるが、但し、AまたはYのうちの少なくとも1つが水素であるものとする、請求項1に記載の方法。
- Zがヒドロキシルまたはメトキシから選択され、Yが水素、ハロゲン、またはカルボン酸から選択され、A、A’、A’’、及びA’’’が独立して、水素及びアミンから選択されるが、但し、A、A’、A’’、及びA’’’のうちの少なくとも1つが第一級または第二級アミンであり、かつAまたはA’’のうちの少なくとも1つが水素であるものとする、請求項1に記載の方法。
- Zがヒドロキシルから選択され、A’がヒドロキシルから選択され、Aが水素であるが、但し、A’’、A’’’、またはYのうちの少なくとも1つが第一級または第二級アミンであるものとする、請求項1に記載の方法。
- Zがヒドロキシルから選択され、A’’’がヒドロキシルから選択され、Yが水素であるが、但し、A、A’、またはA’’のうちの少なくとも1つが第一級または第二級アミンであるものとする、請求項1に記載の方法。
- 前記多官能性アミンモノマーが二官能性アミンである、請求項1に記載の方法。
- 前記対象となるアミン化合物が前記界面重合したポリアミド層にコーティングされ、前記ポリアミド層の表面上に存在する残留酸塩化物基と優先的に反応する、請求項1に記載の方法。
- 前記対象となるアミン化合物が、3,5−ジアミノフェノール、2,4−ジアミノフェノール、3−アミノフェノール、2−アミノフェノール、4−アミノフェノール、5−アミノベンゼン−1,3−ジオール、3−アミノ−5−ヒドロキシ安息香酸、3−アミノ−5−ヒドロキシベンゼンスルホン酸、5−メトキシベンゼン−1,3−ジアミン、4−メトキシベンゼン−1,3−ジアミン、3−メトキシアニリン、2−メトキシアニリン、4−メトキシアニリン、3−アミノ−5−メトキシ安息香酸、3−アミノ−5−メトキシベンゼンスルホン酸、N1,N1−ジメチルベンゼン−1,3−ジアミン、N1,N1−ジメチルベンゼン−1,3,5−トリアミン、N1,N1,N3,N3−テトラメチルベンゼン−1,3,5−トリアミン、N,N’−(5−アミノ−1,3−フェニレン)ビス
(3−オキソブタンアミド)、N−(4−アミノフェニル)−3−オキソブタンアミド、5−アミノ−1,3−フェニレンビス(2,2,2−トリフルオロアセテート)、5−アミノ−1,3−フェニレンジアセテート、3,5−ビス((tert−ブチルジメチルシリル)オキシ)アニリン、(3,5−ビス((tert−ブチルジメチルシリル)オキシ)フェニル)メタンアミン、及び2−(3,5−ビス((tert−ブチルジメチルシリル)オキシ)フェニル)エタンアミンのうちの少なくとも1つから選択される、請求項1に記載の方法。
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JP2017518174A (ja) | 2017-07-06 |
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